


How Do You Sleep? (Part II)

by diamonds_and_rust



Category: Supernatural
Genre: Dom/sub Undertones, F/M, Fluff and Smut, Reader-Insert, Shameless Smut, Spanking
Language: English
Status: Completed
Published: 2015-01-04
Updated: 2015-01-04
Packaged: 2018-03-05 10:33:22
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,653
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3116855
Author URL: https://archiveofourown.org/users/diamonds_and_rust/pseuds/diamonds_and_rust
Summary: <blockquote class="userstuff">
              <p>An even smuttier sequel to the first "How Do You Sleep?". And by "smuttier" I mean my face felt sunburned I was blushing so bad.</p>
            </blockquote>





	How Do You Sleep? (Part II)

The next day was interesting for a few reasons, the most important one being, of course, the fact that you and Henry had spent the night together. You admittedly felt a little smug at having the Winchester all to yourself for an evening. And the brothers were none the wiser. Although that may have been due to the fact that they were still a little hung over.

But it was a surprise when Henry made an announcement around five. “I’m going to be taking your lovely friend out to dinner tonight,” he informed Sam and Dean.

“What?” Sam inquired, blinking in surprise.

Henry stood his ground. “I’d invite you, boys, but I’m afraid the activities planned for the night are not family-oriented.”

Meanwhile, you were cracking up. “Oh, so now I’ve upgraded to those mature games?” you teased. “I guess that means we’re playing hangman. Been waiting for this for a while now!” Sam peered at you in confusion, trying to figure out what the joke was. Dean’s eyebrows were drawn together and after a moment, they lifted.

“Oh. They fucked,” he announced.

“Damn it, Dean,” you sighed, taking on a sardonic tone. “This is why you’re my least favorite. You can’t just guess at what happened.”

Henry had a more serious reaction. “That’s none of your business,” he warned.

Dean held up his hands. “Hey, I ain’t judging. It’s just that… I dunno. It’s weird. You’re our grandfather and she’s our friend,” he explained. “I’m gonna need so much mind bleach to get that image out of my head.”

On that lovely note, the conversation was over. You and Henry were out the door, on your way to a local restaurant. It wasn’t fancy, rather it was family-oriented. But it could have been the middle of an arctic tundra and you wouldn’t have minded, so long as you were with Henry.

After the waitress left with your orders, Henry cleared his throat. “I’d like to apologize for my, er, less than respectable behavior last night,” he began, straightening his suit jacket. “I want you to know that to know that was a rare display of passion.”

That made you blink and tilt your head in confusion. “You don’t have to apologize for that. I was delighted with the outcome.”

“I find myself unable to disagree with that assessment,” he replied wryly. “But I don’t… I mean, under normal circumstances, dinner would have come first. I would have done things properly the first time around.”

“You’re still such a gentleman,” you remarked with amusement.

He chuckled. “I don’t know who you’ve been dealing with, but if I’m the nicest man you’ve met in a while, they couldn’t have been that great,” Henry asserted.

At this, you shrugged. “Let’s just say a few manners have been forgotten over the past few decades,” you said dryly. “It’s just a little funny because you wouldn’t hurt a fly and I’m a hunter. Hurting things is my job.”

“I’ve been known to take a more dominant nature when the moment calls for it,” he informed you.

You bit your lip, trying not to laugh loudly at the thought of Henry being any sort of dominant. There was a brief glimpse of potential he had shown you last night, but that seemed to be a spur-of-the-moment kind of thing. “Is that so?” you inquired.

He seemed to realize what you were thinking. A roguish smile flickered over his face. “Indeed. Which brings me to my confession: Tonight I’m afraid that I’m going to have to abandon that gentleman persona for a more audacious one. It’s a matter of pride, admittedly, but it also has a good deal to do with the fact that you’re beautiful when you’re  
“You won’t find me complaining,” you smirked, taking a sip of water from your glass.

Henry leaned forward conspiratorially. “How do you feel about derogatory name calling?” he questioned quietly.

“I’m, uh, not against it if you’re talking about in the bedroom, but if you mean it, then we have a problem,” you laughed despite the seriousness of your words.  
“Of course I wouldn’t mean it,” he assured, appearing to be offended at the mere thought. “You’re a goddess among mortals.”

You rolled your eyes playfully. “Yeah, yeah, quit trying to butter me up.”

By the time the meal was paid for, a knot of anticipation had knotted itself in your stomach. The rest of dinner had been a constant switch between flirting and serious conversation, both tones causing an overall sense of eagerness. You let Henry drive to the motel, but he insisted on holding your hand all throughout the ride. It was a nice and unexpected gesture. The parking lot was devoid of the Impala. The brothers apparently had the good sense to leave before you had returned.

The motel room was dark, and Henry didn’t turn on the main light, instead opting for the softer glow of the lamp on the nightstand. You waited patiently for him to take the lead since that seemed to be his intent. He stepped in front of you and pulled you into a gentle kiss. He drew back a little. “Strip down,” he ordered coolly. “Leave your bra and panties on.”

“Sir, yes, sir,” you mumbled to yourself, hiding a smile as you did what you were told. A shudder ran through you when the cold air hit your body, but you didn’t dare cover up with a blanket. Henry’s gentlemanly behavior would fall through and you’d be warm soon enough.

You clasped your hands behind your back while Henry began to shrug off his blue suit jacket. “By the time I’m done with you, you won’t be able to think about another man,” he stated. He reached to undo his belt. That’s where he paused. He held the somewhat worn strip in his hands in contemplation. “Let’s see, would I rather restrain you with this or spank you?”

“Um, are you looking for a second opinion? Because I have an opinion,” you spoke up helpfully.

His let out a huff of laughter before he took you by the shoulders and sat you down on the bed. He bent forward, his face inches away from yours. “I didn’t ask for your opinion, whore,” he noted. “It would become you to remain silent unless I tell you otherwise. Do you understand?”

Oh, so that’s what he had meant by ‘derogatory’. If you weren’t trying to hold back a whimper, you would have smiled. Instead, you nodded wordlessly in response to his question. The man hadn’t even touched you yet and you were already squirming for him. This assertive side of Henry was quite attractive.

“I am tempted to teach you manners,” he stated, an edge of humor to his tone. “But what good are manners to a whore? Lucky for you that I happen to be in a good mood this evening. Now hold out your hands.” You obeyed, breath hitching when he tugged on the belt once for good measure. Sufficiently bound for his purposes, Henry knelt in front of you. He placed a hand on each knee and slid his hands up the insides of your thighs, taking his time.

He spoke softly, “White panties, huh? Such a pure color for such a dirty girl, don’t you think?” It didn’t matter what you thought because his fingers were an inch away from exactly where you wanted them. “How bad do you want me to touch you?”

“Damn it, Henry, just do it already,” you hissed, your hips rocking forward. His hands disappeared suddenly. You opened your eyes to see a very disapproving man between your legs. “I’m sorry, I mean…”

He placed a hand over your mouth. “Perhaps a lesson in manners is needed after all,” he observed, standing up.

You didn’t reply, a grimace of frustration on your face. He flashed you a reassuring smile. “What kind of lesson?” you asked suspiciously.

“Oh, I meant what I said earlier. I’m definitely spanking you,” Henry said mischievously. “Here, trade places with me.”

You scrambled up, pulse increasing drastically. Henry’s idea of foreplay was certainly interesting, to say the least. You couldn’t help thinking you unleashed a monster. He grabbed your wrists and tugged you onto his lap, your stomach stealing the warmth from the top of his thighs. Henry trailed a finger down your spine, massaging out the knotted muscles. You almost fell into a lull until his other hand smacked your ass.

You gasped in surprise, a new jolt of electricity running through you. This kind of punishment you could get into. The next blow was harder, but that was fine with you. A little pain mixed in with pleasure never hurt anyone. “Henry!” you cried out upon the next smack.

“Yes?” he asked, infuriatingly calm for someone with a desperate woman in his hands.

“What do I have to do?” you begged. He didn’t reply right away, opting to change the spot he struck with his hand. He chose your inner thigh. You mewled and rocked your hips forward.

He soothed the stinging skin with his fingers. “Well, you could let me do what I want to your gorgeous body,” he said thoughtfully. “But you already gave me permission to do that. So why don’t you let me worry about what I want you to do?”

You let out a small noise, squeezing your eyes tightly shut. He was going to drive you crazy. Before you could do anything else, Henry took mercy on you and yanked your panties down, roughly inserting two fingers inside you. The sense of relief you felt was quickly replaced with a sense of intense need. You clenched around the digits tightly. Before you could find release, he pulled out.

A slew of curses ran through your head. “Oh, come on,” you complained under your breath.

“I’m not sure why you’re complaining,” Henry remarked. “I’m going to give you what you want. You’re a very ungrateful slut.” You moaned, sliding off his lap unsteadily. You felt a blush creep up your cheeks. He grabbed your chin and ran his tongue over your bottom lip. You parted your lips willingly, deepening the kiss. Gathering you into his arms, Henry placed you back on the edge of the bed.

Taking a breath, you asked, “Would you mind taking off the belt? I can’t feel my fingers.” A look of surprise flashed over his face, but he didn’t hesitate to remove the restraint. His thumbs helped rub circulation back into your hands.

“Sorry,” he murmured, pushing your hair back so he could kiss your neck. “Forgot that was there.”

You ran your fingers through his hair, tilting your head back in order to give him better access to the skin of your throat. “It’s fine,” you answered breathlessly. Henry trailed his hands up your sides and reached around your back to unclasp your bra. The straps slid down your arms without prompting, your breasts spilling out over the cups.

Henry exhaled heavily, his eyes darkening noticeably. “I spent so much time trying to punish you that I completely neglected two very important aspects of this body of yours,” he lamented, his palms encompassing each breast. You arched your back into his touch, grabbing his wrists and applying more force. He squeezed a nipple, eliciting a strangled cry from you. He rolled it between his finger and thumb. Henry, pleased with the results, applied his mouth to the other one.

His free hand slipped down between your thighs and stroked there. You stopped breathing, awash in so many sensations at once. Your mind raced as he paid homage to your body, one inch at a time. The only thing that you could do was abruptly inform him, “You have too many clothes on! Henry! Henry, please, slow down a minute.”

Ever the gentleman, he ceased his attentions. “Is everything okay?” he inquired, worry clouding his face.

"I'm feeling very vulnerable here, naked all by myself," you explained as you tugged at his shirt. "Take this off. Now."  
He raised an eyebrow, but smirked. "Yes, ma'am," he confirmed. After removing his clothing, he asked, "Is this better? Do you feel better now?"

"Mm, I wouldn't say 'better', but the view has definitely improved," you replied dryly. 

"In that case, you won't mind if I do this." 

Before you could inquire as to what he meant, Henry spread your legs apart before burying his face there. His tongue flicked over your clit, giving you a sharper wave of pleasure. Teeth nipped at sensitive skin and you barely contained a desperate sob. There was a pause. “Did I hurt you?” he asked anxiously.

You shook your head frantically. “Henry, please…,” you pleaded. “Stop torturing me.”

Satisfied that you weren’t in any actual pain, he returned to his administrations. He licked at your wetness experimentally before setting a very thorough pace. You couldn’t stop any sounds that came from your throat. If he hadn’t been holding down your hips, you would’ve been twitching uncontrollably. You threw your head back onto the pillows, gritting your teeth as you came hard on his tongue. He kept lapping with fervency until you calmed down. 

He looked up at you, panting laboriously. “Fuck,” he snarled, surging upwards until he was plundering your mouth and his cock was sliding into you. He hissed in a breath upon entering you. “God, do you know how wet you are?”

You whimpered in response, hooking your legs around his waist, changing the angle of his thrusts. He grasped your left hip and used it to help himself slam into you harder. He quickly hit his release, pressing his face in your neck and letting out a muffled roar. Then, for the second time that evening, you came –and hard. Your nails scored the skin on his back as you came down from your high. The two of you lay there for a few minutes, gasping in ragged breaths.

You momentarily lost track of time and consciousness, so tired as you were. When your eyes fluttered open again, you found yourself cuddled up under a blanket with Henry. His eyes were closed still, but you knew he was awake by the slow grin that was spreading across his lips.

“You’re a jerk,” you giggled quietly, pressing your mouth to his cheek. “The girl’s in 1958 don’t know what they’re missing out on.”

"They're nothing in comparison to you," he answered. The hand resting on your waist pulled you closer. After a moment, he opened his eyes, his gaze searching. "Are you all right? I didn't hurt you, did I?"

You smiled. "No, not at all. You worry too much," you teased. 

Deciding that you were being honest, Henry closed his eyes again. "Hmm, that might be true," he agreed. "But better safe than sorry. You seemed to be a little scared."

"Scared? Of you?" you huffed. "The only scared I am when it comes to you is losing you." 

He was silent for a minute, and you had started to wonder if he had fallen asleep, but then he replied, “I can promise you that as long as it’s within my power, you won’t lose me, sweetheart. You don’t have to worry about that.” 

With a start you realized that you had come to love Henry. It was no longer a friends-turned-lovers relationship. “Damn it, Henry,” you muttered.

“What?”

“I accidentally have started loving you and I’m an idiot.” You wrinkled your nose and sighing. That was the worst thing that could have happened. A serious relationship with him just wasn’t feasible, especially since he probably thought you were being an emotional girl for admitting your affections.

He propped himself on his elbow, frowning down at you. “If your definition of an idiot is someone in love, then count me in,” he countered. 

Huh. Imagine that.

“Let’s be idiots together, then.”


End file.
